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Publication numberUS1001325 A
Publication typeGrant
Publication dateAug 22, 1911
Filing dateNov 2, 1910
Priority dateNov 2, 1910
Publication numberUS 1001325 A, US 1001325A, US-A-1001325, US1001325 A, US1001325A
InventorsFritz Ullmann
Original AssigneeAgfa Ag
Export CitationBiBTeX, EndNote, RefMan
External Links: USPTO, USPTO Assignment, Espacenet
Product of the anthraquinone series and process of making same.
US 1001325 A
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Description  (OCR text may contain errors)

UNITED. STATES mm OFFICE.

FRITZ ULLMANN, or cHAnLorrnNBUnc, GERMANY, ASSIGNOR To Ac'rIEN GESELL- scnu'r Fun ANIL'IN FABRIKATION, or BERLIN, GERMANY.

PRODUCT F 'ISHE ANTHRAQUINONE SERIES AND PROCESS OFMAKING SAME.

1,001,325. No Drawing.

Patented Aug. 22, 1911.

To all whom 'it may concern: Be it known that I, FRITZ ULLMANLN, a subject of the King of Bavaria, residing at Charlottenburg, near Berlin, Germany, my post-ofiice'address being Schillerstrasse 15/16, Charlottenburg', near Berlin, Germany,lhave invented certain new and useful Improvements in New Products of the An ,thraquinone Series andProcesses of Making the Same, of which the following is a speci fication.

My present invention relates to new products of the anthraquinone series and the process for the manufacture of the same consists in acting upon an anthraquinonealpha-carboxylic'acid, that is .to say upon I or a derivative of this acid, with a hydrazin, such as, for instance .phenylhydrazin or bromphenylhydrazin, etc. The reaction which is the base of my invention appears to take place according to the following equation coon +mn. NH. 0. V i N-om,

I 0 i I 00 starting for instance from antraquinone" allpha-carboxylic acid and phenylhydrazin. T ese new bodies may serve as intermediate roductsffor the manufacture of dyesor as of reaction may be altered within widelimr to'be obtained.

. tained bf'imcting solves, then after some time the product of acid-the product dissolves to an orange so lution having a weak green fluorescence.

'It is obvious that my present invention is not limited to the foregoing example or to the details given therein; Thus, for instance, instead of phenylhydraz'in I can employ phen'ylhydrazin-sulfonic acid or bromphenylhydrazin' or hydrazin' itself, etc. Furthermore for the anthraquinone-alphacarbonylic acid used in the above example I can substitute for instance lA-chloi'a'nthraquinone carboxylic acid. or Lfi-nitro- 7.5,

- anthraquinone carboxylic-acid or the chloridof anthraquinone-alpha-carboxylic acid, etc.-

In using such other parent materials for'my,

new process, ofcourse, the special conditions its, without departing from the scope ofmy invention, according to the] nature of the parent materials as well as of the products Having now describedliny'invention-and" the mannerlin which it ma'yperformed What I claim, is,"

1. As new articles of manutactu'r'e the new products of the anthraquinone series, L y

;having. the general formula:

. 1(. to L .95

in'which formula It means a non-metallic substituent', which new products'ma'y be obwitlra hydrazin-upon .a'n anthraquinon'e-a ph-a-carbo lic acid, these Y new products bem in the shape when pulverized, yellowlsh to yel ow powders, very difiicult y soluble in alcohol and ether and soluble in lp' 'vridin.to a yellow solution, whereas they issolvein concentrated sul- {uric acid to a yellow to an orange solution v havin a weak fluorescence.

new articles of manufacture the new roducts of the anthraquinone series, havmg the general formula:

upon an anthraquinone-alpha-carboxylic acid, these new products being in the dry shape when pulverized, yellowish to yellow powders,- very diflicultly soluble in alcohol and ether and soluble in pyridin to-a yellow solution, whereas they dissolve in concentrated sulfuric acid to a yellow to an orange solution having a weakfluorescence.

3. As a new article of manufacture thev new' product of the anthraquinone series, having the formula:

k/ which new product may he obtained by acting with phenylhydrazinupon an anthraqu1nonealphacarboxylic acid, this new product being in the dry shape when pulverized, a yellowish to yellow powder, very diificultly soluble in alcohol and ether and soluble in pyridin to a yellow solution, whereas it dissolves in concentrated sulfuric acid to a yellow to an orange solution having a weak fluorescence.

In testimony whereof I have hereunto set my hand in presence of two subscribing witnesses.

FRITZ ULLMANN.

, WVitnesses:

HENRY HASPER, WOLDEMAR HAUPT.

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US6346536Sep 3, 1997Feb 12, 2002Guilford Pharmaceuticals Inc.Benzopyranoisoquinolone derivatives; neurodegenerative and brain disorders; reperfusion injuries; antiischemic agents
US6348475Jun 1, 2001Feb 19, 2002Guilford Pharmaceuticals Inc.Methods, compounds and compositions for treating gout
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US6387902Dec 31, 1998May 14, 2002Guilford Pharmaceuticals, Inc.Phenazine compounds, methods and pharmaceutical compositions for inhibiting PARP
US6395749Sep 1, 1998May 28, 2002Guilford Pharmaceuticals Inc.Carboxamide compounds, methods, and compositions for inhibiting PARP activity
US6426415May 15, 1998Jul 30, 2002Guilford Pharmaceuticals Inc.Polyadenosine 5'-diphospho-ribose polymerase (parp) enzyme inhibitors, alkoxy substituted n-heterocycle derivatives
US6514983Sep 1, 1998Feb 4, 2003Guilford Pharmaceuticals Inc.Inhibitors of the nucleic enzyme poly(adenosine 5'-diphospho-ribose)polymerase
US6545011Jul 2, 2001Apr 8, 2003Guilford Pharmaceuticals Inc.PARP (poly(adenosine 5'-diphospho-ribose) polymerase) inhibitors
US6635642Sep 1, 1998Oct 21, 2003Guilford Pharmaceuticals Inc.Poly(ADP-ribose) polymerase inhibitors; tissue damage treatment
US6716828Feb 13, 2001Apr 6, 2004Guilford Pharmaceuticals, Inc.Treatment or prevention of neural or cardiovascular tissue damage related to cerebral ischemia and reperfusion injury in an animal by administering poly(adp- ribose) polymerase (?parp?) inhibitors.
US6723733May 15, 2001Apr 20, 2004Guilford Pharmaceuticals, Inc.Polymerase inhibitor
US7307080Feb 6, 2004Dec 11, 2007Mgi Gp, Inc.Nuclear enzyme poly(adenosine 5'-diphospho-ribose) polymerase inhibitors; protection against ill effects of reactive free radicals and nitric oxide
Classifications
U.S. Classification544/233
Cooperative ClassificationC07D487/04